


Working Girl

by Lopsided_Whiskey_Grin



Category: The Flash (TV 2014)
Genre: Bisexual Character, Blow Jobs, Caitlin is a grad student, Double Penetration, Double Penetration in One Hole, Explicit Sexual Content, First Time, Loss of Virginity, Mildly Dubious Consent, Multi, Pre-Series, Sex for Money, Threesome - F/M/M, Underage - Freeform
Language: English
Status: Completed
Published: 2015-01-09
Updated: 2015-01-09
Packaged: 2018-03-06 18:50:36
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 3,602
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3144800
Author URL: https://archiveofourown.org/users/Lopsided_Whiskey_Grin/pseuds/Lopsided_Whiskey_Grin
Summary: <blockquote class="userstuff">
              <p>It was no secret that college was expensive as hell, especially for a girl working her way toward a doctorate in bio-engineering. It was a secret however, how Caitlin Snow earned the money it took to pay off her monumental tuition bills every month without having to take out student loans, and having sex for money was a job Caitlin kept well hidden.</p>
            </blockquote>





	Working Girl

**Author's Note:**

> This was completed as a prompt from a reader. Enjoy ^_^

It was no secret that college was expensive as hell, especially for a girl working her way toward a doctorate in bio-engineering. It _was_ a secret however, how Caitlin Snow earned the money it took to pay off her monumental tuition bills every month without having to take out student loans, and having sex for money was a job Caitlin kept well hidden.

The clients she entertained paid well, _exceptionally_ well, but Caitlin just couldn’t quite bring herself to use the word _prostitute_ , and _hooker_ didn't seem to fit right, so she simply settled for _escort_ as a somewhat suitable label, thought that didn’t precisely match either. She was just a hardworking college student in desperate need of a little extra money, so where was the harm? It wasn’t as if it was  _that_ terrible of a job anyways. And that was the the thing that surprised Catilin the most: she actually really enjoyed it. She hadn't exactly considered herself an overly sexual person, having had only a handful of partners before entering her graduate college studies, but the thrill of being desired, along with the ridiculous amounts of money she earned, made it the best job she’d ever had, and it was a job could she do and do damn well.

She had many repeat clients, mostly older businessmen and city officials, but she occasionally entertained professors and even other students from the university she attended. Men, women, it didn't matter to her, as long as she got paid and both her and her client got off. The one requirement she demanded, however, was complete and utter confidentiality for her client's sake as well her own, only allowing for plans to be made over text messages and never in person. She didn't mind gaining new clients through word of mouth, but she absolutely did not want to be approached face to face.

That was why it was so unnerving when Caitlin overheard a conversation about her, whispered in hushed voices from around the corner of a large metal bookcase in the mostly deserted basement of the sciences library where she sat studying a clinical research essay. She cocked her head to the side, pushing a lock of burnished auburn hair behind her ear as she listened with building annoyance to what sounded an awful lot like two teenage boys about to try and strike up a deal with her.

“That's _her_. I'm telling you, man. I heard my brother's friend talking about how fucking awesome she is," Boy One said with a soft tone of wonder.

Boy Two snickered and Caitlin felt her annoyance boil over into full blown indignation. "You sure he didn't say that she's just an awesome fuck?"

Caitlin had heard enough. She pushed to her feet roughly and rounded the bookshelf within the span of a fraction of a second. Two wide pairs of shocked eyes stared back at her when she came to a stop, crossing her arms and centering a narrowed gaze on the two teenagers. They were both about the same height, standing well above Caitlin's relatively short stature and she gauged them both to be a little over 6 feet.

"You kiss your mother with that mouth?" she hissed, looking from one boy to the other.

The teenager to her left, with brown hair and hazel eyes, had the good grace to at least look embarrassed. A blush raced across his cheeks and he hung his head down. "No ma'am, sorry."

Caitlin pursed her lips and looked over at the second boy. He brushed a lock of black hair up off his forehead before he shoved his hands in his pockets but he kept his mouth shut, his blue eyes shining at her in an almost challenging way.

She glanced back to the first teenager. "How did you find out about me?" she asked, her voice holding a level tone of barely restrained fury.

He brought his head up to look at her, his throat working as he swallowed. “My brother goes to this school and his friend was telling him about you. I overheard them talking."

"And did you also overhear that I don't make any plans in _person_?" She tapped her foot,  awaiting their answer.

Boy Two remained tight lipped, but Boy One shook his head. “No ma'am."

"Well, now you know," she said with a terse nod. "And you can go ahead and forget that you ever heard about me at all."

She turned to go, but Boy Two suddenly spoke up. "So that's it then? We came all the way down here for fucking nothing?

Catlin turned back slowly, her deep brown eyes narrowed to slits. “How old are you?"

Boy Two tilted his chin up. "Fifteen."

Caitlin looked to the second kid, waiting. He was staring at his friend, lips parted slightly in an expression that Caitlin did not entirely understand. He whipped his head back to the front when he realized Caitlin was waiting for his answer. "Fifteen, ma'am," he finally said, blushing again.

"Look," Boy Two, said abruptly, digging into the back pocket of his dark wash jeans and producing a thick stack of fifty dollar bills. "We've been saving up. Are you really gonna fuckin’ turn us away?”

Caitlin glanced down to the money in his hand, quickly calculating it to be five-thousand, and looked back up. That much could actually cover a large chunk of this semester’s tuition costs and might help to partially fund a new electron microscope for the science lab.

She considered the offer carefully for a moment before speaking, “You do know cursing like that is a really dirty habit, don’t you?” she asked in lieu of a direct answer, referring instead to the profanity he’d used for the third time in a row. It was a habit Caitlin suddenly wanted to break him of, and she’d definitely be making him pay for the privilege.

Boy One blinked at her owlishly but Boy Two only smirked. “What, you mean the word _fuck_?” he asked, enunciating the offending expletive.

The corner of Caitlin’s lips turned up in a wicked smile. _Oh, this was going to be fun._

“You two are going to meet me at room 470 in the Wyndham Hotel in exactly one hour.” Boy One whipped out his cell phone and furiously typed in the instructions. “Not one minute late, not one minute early. Or else the whole thing’s off.”

She didn’t even wait for them to reply, just simply turned and walked away. Either they’d come to the hotel or they wouldn’t, but she was pretty positive they would come, and when they did she’d _really_ make them come.

*************************

Caitlin was fixing her hair in the hotel room’s bathroom mirror precisely one hour later when she heard a tentative knock sound at the door. She smiled at her reflection, letting her soft brown tresses fall from her hands and cascade down around her shoulders, and took one last accessing look in the mirror at her tight black dress, feeling the silky slide of her black lace panties and bra hiding under the confining material. Pleased, she turned away from the mirror and left the bathroom, making her way across the spacious en suite sitting room and stopping at the door.

She opened it slowly to reveal Boy One and Boy Two, both looking a bit nervous, but where Boy One made no real attempt to hide that subtle edginess, Boy Two was masking it outright with an overconfident grin.

Caitlin smiled. “Hello, boys,” she said, “Glad you could make it.”

She stepped back from the door, gesturing for them to enter. Boy Two, with his blue eyes clashing beautifully with his dark hair, hesitated. “Should I just wait out here?” he asked, uncertainty revealing a fraction of his hidden nervousness. “I don’t mind if Kyle goes first.”

Caitlin paused, looking between the two as they stood in the hallway. Boy One, Kyle, seemed disappointed by his friend’s offer to stay outside, glancing over at him with his mouth twitching into a frown; Boy Two was completely oblivious to it.

Understanding suddenly dawned on Caitlin as she watched the silent interaction and she was amazed at how she hadn’t noticed this nuance back at the library; Kyle had a huge crush on Boy Two and Boy Two had no idea at all. _Well, this changes things_ , she thought to herself, suddenly deciding she was going to be playing matchmaker in addition to her other duties tonight.

Her smile broadened and she shook her head slowly. “You’re not going anywhere,” she said, pointing at Boy Two. She saw Kyle grin happily out of the corner of her eye when Boy Two shrugged and walked into the room.

Caitlin closed the door after they had entered and turned back toward them as they came to a stop in the middle of the large sitting room. They were both quiet, waiting expectantly for her instructions. It was at this point that most of Caitlin's clients would already be undressed and lying on the bed, but it was pretty obvious from the fact that they were still clothed and looking around the room like little lost puppies that this was going to the first time for both of them and they needed as much direction as possible.

She sauntered across the room, her hands planted on her hips. "Boy Two," she began addressing him.

His blue eyes flashed almost indignantly. "My name is Brendon," he said, crossing his arms over his chest. "And I'm not a fucking _boy_. I'll be sixteen in four days."

Catlin came to a stop before him and swiftly brought her hand up, cupping his jaw firmly and tilting his head down with a rough yank. "I think you already know how I feel about cursing, _Brendon_."  His blue eyes widened at her serious tone. “So, until _you_ can learn not to use that foul language, _I'm_ not going to let you come. Do you understand?"

Brendon's eyes darkened in a flush of arousal, but he nodded.

Caitlin released his chin and took a step back. "Good," she said, satisfied. "Now I want the both of you to undress each other."

Kyle grinned eagerly and quickly turned toward his friend. Brendon looked a little uncertain at first, but did as he was told, reaching out to unzip Kyle's black hoodie and helping to tug it from his shoulders. Kyle's hands immediately went for the buttons of Brendon's fly, popping them open with a tender reverence that did not go unnoticed by Caitlin in the least.

After they had shed all of their clothes and stood before her, clearly excited and very aroused, Caitlin, still fully dressed even down to her stilettos, sunk to her knees on the plush carpet. "Come here," she beckoned. "I'm going to get things started by sucking your cocks."

"Both at the same time?" Brendon asked, doubt coloring his voice.

Caitlin craned her neck up to look at him, leveling her brown eyes at him in a frank stare. "When will you learn to stop asking so many questions? Get over here."

They complied, wordlessly stepping forward. She reached her hands out, maneuvering them slightly so that they were hip to hip but angled enough toward each other that she was able to press their hardened cocks together. She looked up, licking over both heads then stretched her lips around them, stuffing the members as far into her mouth as she could before pulling back and off. She then swallowed down Brendon's cock, making sure to coat the entire length in a thick layer of saliva before releasing him from the wet heat of her mouth.

Brendon groaned loudly and she smiled to herself at how quickly she was able to pull him out of his quietly skeptical shell. She then moved onto Kyle next, drawing him into her mouth slowly. He looked down at her, his eyes glazing over in pleasure as she licked a long, wet stripe up the underside of his thick cock.

She released him after a moment, bringing her hands up to grip both dicks together and guided them to pump into the channel of her fists in an opposing rhythm while still allowing their hardened lengths to slide against each other with each thrust. She looked up, seeing Kyle's head fall back in pure bliss and knew the pleasure she was giving him was only part of it; the sensation of Brendon's cock sliding against his was probably something he had dreamed about for a long time.

Caitlin glanced over to Brendon, bringing her mouth forward to swallow him down again, fully understanding that the sensation that Kyle had savored, of his friend's dick slipping against his own, was giving _Brendon_ pleasure too, something he had probably not even considered before but was enjoying immensely nonetheless.

"Fuck," Brendon whispered hoarsely.

Catlin immediately pulled off his cock, wrapping her fingers tightly around the base of Brendon's dick. He yelped and looked down.

"Language," Caitlin warned, bringing her free hand up to wipe the sheen of her own saliva from her chin.

Brendon nodded briskly, awe clear on his face. “Sorry, I forgot."

Caitlin smiled, silently accepting his apology, and jerked her head toward the large king size bed across the room. “Kyle, you go lay down up by the headboard, and Brendon, you sit there on the end until I tell you what to do.”

Both complied while Caitlin gained her footing and began unzipping her dress. She let it fall to the floor then stepped out of her shoes and lingerie while both boys watched raptly.

They continued to stare, Kyle with his back propped up against the headboard and Brendon kneeling on the end of the bed, as she grabbed two condoms off of the dresser beside her. She climbed up onto the bed, helping first Brendon and then Kyle to put them on.

That done, she crawled even closer to Kyle, tugging him down to lay back on the bed and straddled his hips. He stared up at her, cheeks and chest flushed with arousal. Caitlin smiled and curled forward, rubbing the wet heat of her sex against Kyle’s hardened cock, and pressed a deep kiss to his parted lips. He was frozen still for a moment before Caitlin slipped her tongue up against his and then he finally got with the program, returning her kiss with a sloppy but endearing hunger.

She pulled back after a moment, both of them gasping for breath, and cast a glance back over her shoulder to Brendon kneeling behind her. “Feel free to touch now, Brendon,” she said, arching a delicate eyebrow.

Brendon swallowed and slowly nodded, his eyes roaming over her naked back, seemingly deciding what he wanted to do first. He lunged forward after he’d made up his mind, wrapping his arms around Caitlin’s middle, bringing his hands up to cup and knead her breasts. Caitlin let out a breathy moan and turned her head to the side to accept the awkward kiss Brendon pressed to the side of her mouth.

Brendon continued to grope and paw at her with a gentle fervor and she leaned forward toward Kyle again. His hazel eyes were blown nearly to black with arousal as he looked up at Caitlin and Brendon behind her. Caitlin reached for Kyle’s hands where they were fisting into the sheets beneath him and tugged one down to her pussy, guiding his fingers to her slick core. She brought his other hand up over her shoulder to caress the side of Brendon’s face just behind her. Brendon groaned at the touch, not once flinching away even as he must have surely seen that it was his friend’s hand and not Caitlin’s that was stroking his cheek and hair.

Caitlin smiled happily, feeling the feather-light touches Kyle was pressing into her drag her closer and closer to exploding. She reached down, gently brushing his hand away and wrapping her fingers around his straining cock and centering it at her entrance. She leaned forward even more, sliding down onto him and pressing her breasts against his heaving chest. Kyle’s eyes squeezed shut and his hands came down to grip tightly at her hips. She moved up and down on his dick a few times, riding him in a pleasurable slide before feeling the restless movements of Brendon at her back.  

Caitlin craned her neck to the side, looking over her shoulder at him. “Join in on the fun,” she rasped with a grin. “There’s enough room for both of you, don’t worry,” she said, quickly curtailing any questions he might have.

Her eyelids fluttered shut when she felt Brendon stretching out over her back, pressing his cock inside her slowly right alongside Kyle’s, which was still pumping in and out of her with a breathtaking rapidness. Brendon was soon fully buried and all three of them gasped with how perfect it felt.

And then the two boys found a rhythm, both thrusting into her deeply, and Caitlin was nearly lost to the pleasure flooding through her. It had been a long time since she had felt so utterly _full_. She blinked her eyes open, looking down at Kyle panting beneath her, watching how intensely he was staring at Brendon over her shoulder. She dropped her head forward slightly, aligning her mouth with the soft cup of Kyle’s ear. “Kiss him,” she whispered. She felt Kyle nod fervently, the perspiration on his cheek sliding against hers warmly.

Kyle reached his hand back up to Brendon’s head, tangling his fingers in the dark locks of his friend’s hair and tugging him close. Caitlin was smashed between the two as Kyle crashed his lips up against Brendon’s mouth. Neither of them broke the pounding pace they had originally set, even as Brendon let out a surprised moan.

Caitlin grinned to herself at her newfound talent for matchmaking and angled her hips downward so that she could rub her clit up against Kyle beneath her as he continued to thrust into her heated and throbbing core. A tight coil of arousal wound low in her belly, signaling her rapidly approaching orgasm and she quickened the snap of her hips. And judging by the suddenly erratic movements of both boys, they were going to be following her right over the edge any moment.

Kyle continued to assault Brendon’s mouth, visibly thrusting his tongue in deep, and Caitlin found she could not look away from the passion unfolding between the two right before her eyes. Her orgasm suddenly slammed through her as she watched the boys kiss and she shuddered violently between them, crying out hoarsely. Her pussy clenched around both cocks inside her, shoving Kyle and Brendon off the precipice of release as well.

Brendon tore his mouth away from Kyle’s lips, groaning loudly, filling the condom inside Caitlin in a warm rush just as Kyle did the same. Caitlin marveled at how it happened damn near simultaneously.

The three suddenly fell quiet and still for a few moments, except for the panting breaths and shudders coursing through them, until Caitlin glanced over to Brendon’s face beside hers. “I can’t really breathe,” she chuckled, trying to tear the boy’s attention away from each other.

“Oh, fu-... I mean, sorry!" Brendon exclaimed, pushing off of her back. He pulled out gently, then helped her to sit up after Kyle had pulled his softening cock from her as well.

Caitlin smiled with a shake of her head. “It’s fine,” she said and showed the two how to properly dispose of their used condoms.

She excused herself to the bathroom for a moment to grab her silk robe and when she came back into the bedroom she saw both boys, still naked, intertwined with each other and kissing heatedly on the bed. Clearing her throat, she tied the belt of her robe around her waist as she came to a stop beside the large mattress.

The boys looked up at her sheepishly, Kyle grinning broadly, and a happy blush racing across Brendon’s cheeks. They both climbed off the bed and raced around to where Caitlin was standing, hugging her tightly. She chuckled softly and pulled back after a moment. Kyle was positively beaming as he looked down at her standing before him.

“Thank you,” he said, and the sincerity in his voice touched Caitlin’s heart deeply.

She nodded and then swatted them both on the arm playfully. “Just remember to contact me through a _text_ next time, got it?”

They both voiced their understanding and quickly went about getting dressed. Brendon fished the stack of money out of his jeans after he was fully clothed once again and handed it over to Caitlin with a huge smile curving his lips. Caitlin accepted it gratefully and saw them both to the door, grinning herself when the two walked out hand in hand.

She plopped back down on the bed after locking the door, brushing a lock of auburn hair from her forehead and counting the money. Her phone suddenly chimed a message alert and Caitlin smiled, grabbing it up off the bedside table, absently wondering if it was the boys already asking for round two, but was satisfied nonetheless when she saw that it was someone else, someone she hadn’t done business with before, requesting her services. It was a text that, unbeknownst to her, would literally change her life.

**[text]:** _Hi, my name is Ronnie Raymond and I was wondering if you might be free tomorrow night?_

 

 


End file.
